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Volumn 62, Issue 24, 2006, Pages 5803-5807

A facile method for the synthesis of 1,3-oxathiolan-2-ones by reaction of oxiranes, sulfur, and carbon monoxide

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; CARBON MONOXIDE; ETHYLENE OXIDE DERIVATIVE; SELENIUM; SODIUM DERIVATIVE; SULFUR DERIVATIVE; THIOL DERIVATIVE;

EID: 33646355678     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.03.081     Document Type: Article
Times cited : (17)

References (40)
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    • For recent reviews of carbonylation, see:
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    • (1995) Comprehensive Organometallic Chemistry , vol.12 , pp. 349
    • Bates, R.W.1
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    • 33646383155 scopus 로고    scopus 로고
    • Ethylene-Plastique S. A. BP 1, 1968, 135, 799;
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    • Thiokol Chemical Corp. USP 3, 1966, 240, 788;
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    • Reynolds, D. D. U.S. Patent 2,828,318, 1958;
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    • Chem. Abstr. 52 (1958) 14651
    • (1958) Chem. Abstr. , vol.52 , pp. 14651
  • 21
    • 0242498720 scopus 로고    scopus 로고
    • Oku et al. recently reported the viable utilization of polycarbonate as a phosgene equivalent. In this paper, they have disclosed the reaction of polycarbonate with mercaptoethanol in the presence of a catalytic amount of base giving 1,3-oxathiolan-2-one in good yields. See:
    • Oku et al. recently reported the viable utilization of polycarbonate as a phosgene equivalent. In this paper, they have disclosed the reaction of polycarbonate with mercaptoethanol in the presence of a catalytic amount of base giving 1,3-oxathiolan-2-one in good yields. See:. Hata S., Goto H., Tanaka S., Oku A. J. Appl. Polym. Sci. 90 (2003) 2959
    • (2003) J. Appl. Polym. Sci. , vol.90 , pp. 2959
    • Hata, S.1    Goto, H.2    Tanaka, S.3    Oku, A.4
  • 23
    • 84987529718 scopus 로고
    • We recently showed that the reaction of 2-alkyn-1-ols with sulfur and carbon monoxide in the presence of triethylamine, followed by copper (I)-catalyzed cyclization gave 4-alkylidene-2-oxo-1,3-oxathiolanes in moderate to good yields. See:
    • We recently showed that the reaction of 2-alkyn-1-ols with sulfur and carbon monoxide in the presence of triethylamine, followed by copper (I)-catalyzed cyclization gave 4-alkylidene-2-oxo-1,3-oxathiolanes in moderate to good yields. See:. Mizuno T., Nakamura F., Ishino Y., Nishiguchi I., Hirashima T., Ogawa A., Kambe N., and Sonoda N. Synthesis (1989) 770
    • (1989) Synthesis , pp. 770
    • Mizuno, T.1    Nakamura, F.2    Ishino, Y.3    Nishiguchi, I.4    Hirashima, T.5    Ogawa, A.6    Kambe, N.7    Sonoda, N.8
  • 25
    • 33646378477 scopus 로고    scopus 로고
    • note
    • The effect of various amines on this reaction was also investigated, DBU; 56%, DBN; 23%, N-methylpyrrolidine; 0%, triethylamine; 0%, pyridine; and 0%, NaOH.
  • 26
    • 33646376980 scopus 로고    scopus 로고
    • note
    • Thioformic acid S-benzyl ester was formed in 2% yield by the reaction of sulfur with carbon monoxide in the presence of sodium hydride followed by alkylation with benzyl bromide.
  • 33
    • 33646371297 scopus 로고    scopus 로고
    • note
    • When the reaction solution was oxidized by air, a gray selenium precipitate was recovered by filtration.
  • 34
    • 33646362336 scopus 로고    scopus 로고
    • note
    • It was proposed that the concentration of carbonyl sulfide was increased by the addition of the selenium catalyst. The yield of the 1,3-oxathiolanes was then improved by the promotion of the reaction of the oxiranes with carbonyl sulfide.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.